Maltol
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| Maltol | |
|---|---|
| Image:Maltol.png | |
| IUPAC name | 3-hydroxy-2-methyl-4H-pyran-4-one |
| Identifiers | |
| CAS number | |
| SMILES | O=C1C=COC(C)=C1O |
| Properties | |
| Molecular formula | C6H6O3 |
| Molar mass | 126.11 g/mol |
| Density | 1.348 g/cm3 |
| Melting point |
161-162 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
Maltol is a naturally occurring organic compound that is used primarily as a flavor enhancer. It is found in the bark of larch tree, in pine needles, and in roasted malt (from which it gets its name). It is a white crystalline powder that is soluble in hot water, chloroform, and other polar solvents. Because it has the odor of caramel, maltol is used to impart a sweet aroma to fragrances. Maltol has a taste and odor reminiscent of freshly baked bread, and is used as a flavor enhancer (E number E636) in breads and cakes.
Maltol, like related 3-hydroxy-4-pyrones such as kojic acid, binds to hard metal centers such as Fe3+, Ga3+, Al3+, and VO3+.[1] Related to this property, maltol has been reported to greatly increase aluminium uptake in the body [2] and to increase the oral bioavailability of gallium [3] and iron. [4]
See also
References
- ↑ B. D. Liboiron, K. H. Thompson, G. R. Hanson, E. Lam, N. Aebischer, C. Orvig (2005). "New Insights into the Interactions of Serum Proteins with Bis(maltolato)oxovanadium(IV): Transport and Biotransformation of Insulin-Enhancing Vanadium Pharmaceuticals". J. Am. Chem. Soc. 127: 5104-5115. doi:10.1021/ja043944n.
- ↑ N. Kaneko, H. Yasui, J. Takada, K. Suzuki, H. Sakurai (2004). "Orally administrated aluminum-maltolate complex enhances oxidative stress in the organs of mice". J. Inorg. Biochem. 98: 2022-2031. doi:10.1016/j.jinorgbio.2004.09.008.
- ↑ L. R. Bernstein, T. Tanner, C. Godfrey, B. Noll (2000). "Chemistry and pharmacokinetics of gallium maltolate, a compound with high oral gallium bioavailability". Metal Based Drugs 7: 33-48. doi:10.1155/MBD.2000.33.
- ↑ D.M. Reffitt, T.J. Burden, P.T. Seed, J. Wood J, R.P. Thompson, J.J. Powell (2000). "Assessment of iron absorption from ferric trimaltol". Ann. Clin. Biochem. 37: 457-66.
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